Open AccessHighly Stable Meldrum’s Acid Derivatives for Irreversible Aqueous Covalent Modification of Amines
Author(s) -
Garrett J. Davis,
Holly A. Sofka,
John C. Jewett
Publication year - 2020
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.0c00597
Subject(s) - chemistry , nucleophile , combinatorial chemistry , aqueous solution , covalent bond , lysine , aqueous medium , organic chemistry , amino acid , biochemistry , catalysis
This work describes the development of a highly stable and pH-responsive probe for lysine modification. The scaffold has marked stability in the presence of several biological nucleophiles and across a wide pH range (2-12). Several functional analogs showed robust labeling of a protein at pH > 9. Taken together, our system displays versatility and can be easily adapted for variety of applications, while demonstrating stability suitable for a wide range of biologically compatible systems.